Water → HCID 19101845, compound

HRID 1974572Notes

Reaction equation

HRID 1974572 reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]([C:9]([F:12])([F:11])[F:10])[CH:5]=[C:6]([NH2:8])[CH:7]=1.[CH2:13]([CH:15]1[O:17][CH2:16]1)Cl.[OH2:18].[OH-:19].[Na+]>C(O)C>[CH2:13]([N:1]([CH2:13][CH:15]1[O:17][CH2:16]1)[C:2]1[CH:3]=[C:4]([C:9]([F:10])([F:11])[F:12])[CH:5]=[C:6]([N:8]([CH2:5][CH:4]2[O:19][CH2:9]2)[CH2:7][CH:2]2[O:18][CH2:3]2)[CH:7]=1)[CH:15]1[O:17][CH2:16]1

Participants

6

Reactant 4

HCID 962WaterHCID 7835EpichlorohydrinHCID 14798Sodium HydroxideHCID 677815-(Trifluoromethyl)benzene-1,3-diamine

Product 1

HCID 19101845HCID 19101845, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
80 °C

Procedure

A mixture of 3,5-diaminobenzotrifluoride (116.9 grams, 0.66 moles), epichlorohydrin (491.5 grams, 5.31 moles), water (35 grams) and 95 wt% ethanol (257 grams) was heated in a resin kettle at 80° C. After 6 hours, the temperature was lowered to 60° C. and 30wt% sodium hydroxide solution (445 grams, 3.34 moles) was added over a 1 hour period. The mixture was heated an additional 3.5 hours at 60° C. The volatile components were removed by evaporative distillation at 60° C. and 30 mm. The resin was dissolved in toluene (585 mL) and washed four times with water (750 mL, 500 mL, 500 mL and 500 mL). Removal of the toluene and the residual water by evaporative distillation provided an amber resin (262.3 grams, 98.8 wt%). The weight of the resin per epoxide was 125.6 using the method described by W. Liu, E.M. Pearce and T.K. Kwei; J. Appl. Pol. Sci. 30 2907 (1985). The epoxy content of the 35-DABTF resin sample was 80%.

Workup

  1. customwas lowered to 60° C.
  2. temperatureThe mixture was heated an additional 3.5 hours at 60° C
  3. customThe volatile components were removed by evaporative distillation at 60° C.
  4. dissolutionThe resin was dissolved in toluene (585 mL)
  5. washwashed four times with water (750 mL, 500 mL, 500 mL and 500 mL)
  6. customRemoval of the toluene
  7. distillationthe residual water by evaporative distillation
  8. customprovided an amber resin (262.3 grams, 98.8 wt%)

Sources & evidence

ORD record
ord-bc7e3aafd0c84d08a685eeb0781d0960
Source dataset
uspto-grants-1994_02
Patent number
US05283270

Reaction notes

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